How do I end things with someone I am seeing without disappointing her/hurting feelings?

OK, so I have a big problem with upsetting people/hurting their feelings. I really don't like to do it, so I generally try to please them as much as possible. This plays out in my dating game, because if I start seeing a girl and she likes me a lot, I kind of feel obligated to keep seeing her even if I am not that into her, which I know is bad for both of us.

Usually, I will just let things play out until the girl ends things with me, so that way I don't have to be the one to do it. I realize that I need to work on that though, because that is not a very effective or fair strategy.

So in my current situation, I was seeing a girl I was crazy about, but things didn't work out. Now I'm seeing a new girl, and she seems to be really into me (if only the previous girl could have been into me the way this one is, but alas, that is life). I don't mind her company, and she is nice, intelligent and funny, but I just don't feel a strong desire to keep seeing her, yet I am continuing to do so, mainly out of boredom and the desire to avoid telling her I'm not interested.

So I guess I'd like to hear how you all handle situations like this, what you tell the person, etc. I have told a few girls that I was not interested in the past, but I don't feel like I handled those situations particularly well, and I feel like I let things draw out a little too much for fear of ending them. I figure I should have learned a good way of doing this by now, as it is by far the weakest part of my dating game. Any advice would be appreciated.


Most Helpful Girl

  • I'm the same way. I hate hurting people and will avoid it at all costs. It's not good to lead someone on, but I guess I take the coward's approach in not telling him what I'm really feeling because it's just easier to go with the flow instead of putting an end to things.

    With my ex, he was really into me and he was the sweetest guy in the world. But there was just no chemistry for me. I liked him as a friend. But after a few months of "leading him on", I finally decided to end things by telling him that he's a great person, I'll always care for him and I'll always be there for him. But at this stage in my life, I'm just not ready to be in a relationship. That I wanted to be done with grad school before getting serious with anyone, etc".